1. Field of the Invention
Arylation of olefinic alcohols.
2. Description of the Prior Art
Aromatic rings have heretofore been added to olefinic double bonds by reacting the olefin with an aryl mercuric halide in the presence of a palladium catalyst (R. F. Heck, J. Am. Chem. Soc., 90, 5518-5538 (1968); U.S. Pat. No. 3,767,710). Normally styrene type products are formed. When the original olefinic compound was an allylic alcohol containing hydrogen on the .alpha. carbon atom, aryl substituted aldehydes and ketones were formed in low yield (generally less than 50% of theory). More recently, methods for adding aryl groups to olefins have been reported in which a palladium catalyst is used directly with an aryl iodide or aryl bromide in the presence of reagents and/or co-catalysts such as potassium acetate, tertiary amines and/or triphenylphosphine (R. F. Heck et al., J. Am. Chem. Soc., 96, 1133 (1974); R. F. Heck et al., J. Org. Chem., 37, 2320, (1972); K. Mori et al., Bull Chem. Soc. Japan, 46, 1505 (1973).
There has not been reported a palladium catalyzed reaction of aryl iodides or bromides with olefinic alcohols to provide aryl aldehydes, aryl ketones or aryl olefinic alcohols. The present invention provides for the synthesis of these compounds in high yield.